(S)-2-((S)-6-amino-2-((S)-2-((2S,3R)-2-((S)-2-((2S,3R)-2-decanamido-3-hydroxybutanamido)-3-methylbutanamido)-3-hydroxybutanamido)-3-(4-hydroxyphenyl)propanamido)hexanamido)-3-phenylpropanoic acid

ID: ALA378000

PubChem CID: 44412450

Max Phase: Preclinical

Molecular Formula: C47H73N7O11

Molecular Weight: 912.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)[C@@H](C)O)C(C)C)[C@@H](C)O

Standard InChI:  InChI=1S/C47H73N7O11/c1-6-7-8-9-10-11-15-21-38(58)52-40(30(4)55)46(63)53-39(29(2)3)44(61)54-41(31(5)56)45(62)50-36(27-33-22-24-34(57)25-23-33)43(60)49-35(20-16-17-26-48)42(59)51-37(47(64)65)28-32-18-13-12-14-19-32/h12-14,18-19,22-25,29-31,35-37,39-41,55-57H,6-11,15-17,20-21,26-28,48H2,1-5H3,(H,49,60)(H,50,62)(H,51,59)(H,52,58)(H,53,63)(H,54,61)(H,64,65)/t30-,31-,35+,36+,37+,39+,40+,41+/m1/s1

Standard InChI Key:  CDTGHLYBYSXRGU-RDOWQFMTSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA378000

   (S)-2-((S)-6-amino-2-((S)-2-((2S,3R)-2-((S)-2-((2S,3R)-2-decanamido-3-hydroxybutanamido)-3-methylbutanamido)-3-hydroxybutanamido)-3-(4-hydroxyphenyl)propanamido)hexanamido)-3-phenylpropanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 912.14

Molecular Weight (Monoisotopic): 911.5368

AlogP: 1.86

#Rotatable Bonds: 31

Polar Surface Area: 298.61

Molecular Species: ZWITTERION

HBA: 11

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.70

CX Basic pKa: 17.64

CX LogP: 0.61

CX LogD: 0.61

Aromatic Rings: 2

Heavy Atoms: 65

QED Weighted: 0.05

Np Likeness Score: 0.24

References

1. Basse N, Papapostolou D, Pagano M, Reboud-Ravaux M, Bernard E, Felten AS, Vanderesse R..  (2006)  Development of lipopeptides for inhibiting 20S proteasomes.,  16  (12): [PMID:16630721] [10.1016/j.bmcl.2006.03.033]

Source

Source(1):

• Scientific Literature